Mating Season 2: MILF Madness

• hours later -

After Twilight had cast the cloud-walking spell on him, Spike was once again in Cloudsdale and ready to help yet another MILF with a love issue, although this time it seemed to be more sexually explicit than Miss Shy's "don't make me go outside" problem, this time it was a "help me use my sexy tits" problem. Rainbow walked Spike to the front door of her parents house and said "Thanks for agreeing to help out Spike, I know it's kind of a weird request but this will seriously be a big help. I know I said my dad is cool with my mom having some extra-marital fun every now and then but we've managed to get him out of the house for today because this whole titty fuck thing is technically a birthday surprise so we kinda wanna keep it a secret, got it?"

Spike nodded and said "Happy to help!" Spike was still convinced that all these coincidental situations that basically delivered him sex opportunities with a hot MILF during the mating season must have been the hand of fate at work.

Rainbow knocked on the door for him and said "Well, have fun!" Spike stood there nervously and just as Rainbow had disappeared from view to go and do whatever it is she was planning to do that day, Windy Whistles opened the door and Spike's bottom jaw almost thudded to the ground when he saw just how enormous her tits were. It appeared that Velvet must have been only slightly above average in terms of her body proportions because she lost out on ass size to Pear Butter and now she had lost out on breast size to Windy Whistles, how did Rainbow end up not being so well-endowed in the chest area when her mom had such massive fucking milk jugs? Spike's body responded instantly and he was pretty much almost fully erect before Windy Whistles finally greeted him.

"Hello Spike! Thank you so much for coming over, I don't imagine it's every day that you find yourself in the situation of having to sexually please an older woman!" Spike had to hold back a laugh at that statement, it seemed that mating season provided him that opportunity at a frankly alarming rate. Then WIndy Whistles blushed as she said "Well... I suppose more accurately you're going to be helping me to learn how to sexually pleasure you with my... um, let's say rather ample breasts...", she may have been dodging the exact wording but the message was clear, she knew she had huge melons, they were attached to her after all. Windy cleared her throat and said "Well do come in Spike, quickly if you please, I'd rather not let anyone spot the rather large erection you're sporting and failing to hide from view, you're here to teach me how to deal with your equipment but I'm certainly not getting my tits out to pleasure you right here on my front door step".

Spike blushed and wore a nervous apologetic smile as he entered the house and allowed Windy to close the door before he said "Ha... sorry Windy, it's just that you're um... unexpected I guess? You know... with the whole......"

Windy Whistles interrupted with a smile and said "You mean you weren't expecting Rainbow Dash to have a mother that had a nice fat rack for you to stare at and drool over?" Spike nodded, making Windy chuckle as she said "Yes, large breasts run in the family, although unfortunately for Rainbow it tends to skip a generation, my mother was very flat-chested while my grandmother had very generous breasts, so if Rainbow ever has a daughter then she will end up with massive mammaries the second she hits puberty!" Spike was beginning to feel a little frustrated, all this talk of large breasts was only making his erection stronger, his hormones firing on all cylinders as they screamed "FUCK SOMETHING" at his brain, Windy noticed that Spike was just getting hornier by the second and decided that the time for idle chit-chat was over.

Spike tried to shake off his apprehension and said, as confidently as he could, "So Windy... how do you wanna go about this?"

Windy shrugged and went "You're the one who's gonna be receiving a big titty fuck, you tell me, you're here to teach me how to do it after all"

That was a good point, Spike said "Well, let's start with taking our clothes off and just see where it takes us", Spike took of his shoes and unbuckled his belt to pull his jeans and underwear down, desperate to free his member from the constraints of the fabric it was straining against in an effort to show off just how hard and ready it was for the nearest hole.

As his cock sprung out of his underwear, throbbing and already leaking pre, Windy smirked and said "Impressive, what do you think of these?" Windy punctuated her last word but undoing just two buttons of her shirt and allowing gravity to do the rest as her bare breasts practically bounced out from her shirt, revealing that she hadn't bothered to wear a bra that day. Spike was still mystified at how a woman could have breasts so large and not be suffering from some kind of spinal condition from the weight of them, Windy raised an eyebrow and said "Well? I'm waiting for your opinion Spike..." before gently swaying from side to side, shaking her tits and showing off just how soft and pliable they must have been.

Spike forced himself to speak as the dumbest response ever tumbled out of his face when he said "I... need to cum..." and sat down on the sofa.

Windy let out a giggle and said "Well, that's why you're here I guess" then walked over and sat down on her knees in front of Spike before going "So, show me how to do it, teach me the best way I can empty your balls with my tits"

Spike gulped and said "Um... r-right, well... the best way to start is to get me into your cleavage..."

Windy went "Like this?" Windy was clearly not exactly well versed in the art of boob jobs as she just pushed the front of her breasts against his pulsating prick.

Spike went "No no no... you gotta imagine it like a hot dog, really get my dick deep in between your breasts", Windy gripped her breasts and separated them before successfully sandwiching Spike's cock with them, completing step one of her first foray into getting someone off with her tits. Spike let out a sigh of contentment as he felt the warmth of her soft tit flesh envelope every inch of his dick with just his tip peaking out from the top, then he said "That's good, now move them up and down"

Windy, still not quite grasping how it worked, just moved her torso up and down and got frustrated at Spike's cock continually slipping out of her cleavage every time she tried to move. Spike went "Windy, you gotta hold it in there"

Windy went "But how? My breasts are in the way, I can't get my hands on it with them in the way..."

Spike said "Grab your breasts and squeeze them together, then move up and down", Windy did as he said and was pleasantly surprised this his dick stayed put this time.

Windy was weirdly excited and said "Is... this it? Am I doing it right?"

Spike let out a breath and said "Whoo... yeah, you got the basic idea. Depending on the guy you can increase the speed, maybe move your breasts around as you go up and down, use a little lube to make it slippery, let him control the pace etcetera, but yeah, you're... mmm you are fucking me so good with your tits"

Windy grinned widely and went "Yay! So um... you wanna use my chest to finish yourself off? You can cum on my face if you want..."

Spike's eyes went wide, the switch in his mind from civilized to primal was flicked as, with a toothy wicked smile, he practically growled "Fuck yeah!" Windy let out a yelp as Spike roughly grabbed her tits and started fucking them, thrusting as fast as he could with his hips clapping against the underside of her breasts. Spike's pre created a wet sensation as it ran down his length with Windy's cleavage smothering it over every inch of him, considering it was the mating season and Spike was already close, the tit fucking he delivered didn't last nearly as long as he would have liked. While there was no smoke or fire this time around, Spike groaned as he gave one mighty thrust and blasted cum all over Windy's face, so much so that she had to close her eyes while the excess jizz he squirted all over her face dripped down onto her bust. When Spike finally calmed down, he let go of her breasts and felt a twinge of embarrassment as he saw the copious amount of dragon seed he had painted Windy's face with as she began wiping her face and, in an unexpected move, disposed of the substance by scooping it into her mouth and swallowing it down.

"Well... thank you Spike, I think I can effectively jack off my husband with my tits now..." said Windy, continuing to clean up her face as she buttoned her shirt back up.

Spike put the rest of his clothes back on and said "Yeah... n-no problem, glad to be of service!" Windy bid farewell to Spike with a smile and a wave as he left the house to return home to Twilight, a job well done. When he returned he was almost relieved that Twilight didn't have a sexy surprise in store for him, because the only thing he found worse than struggling to control his urges and resisting temptation was consistently having just a little too much sex to a point where he was constantly exhausted, which he found interesting considering he had quite welcomed and embraced the idea of having three hot MILFs service him every mating season. A couple of days went past with Spike once again being frustrated, fighting against his own body and managing to avoid any sexual encounters with Twilight for once, his balls stayed very full and his need to fuck only got stronger, never seeming to level out.

On the third day after having taught Windy Whistles to tit fuck, a small distraction appeared in the form of a knocking at the front door. As Spike dragged his lazy lizard body over to the door, he got the shock of his life when he opened the door and suddenly found himself immediately on the floor with his vision entirely taken up by the familiar face of Pinkie Pie. "HeySpikehow'sitgoing!?Youhavingagoodday!?IknowIam!It'sbeensuchalongtimesinceI'veseenyou!Iheardit'sthematingseasonfordragonsatthemoment,howyoufindingit!?Iimagineit'skindafrustratingsincetherearenogirldragonsaroundhuh!?Hopefullyyou'regettingplentyofactionfromalltheMILFsyou'vebeenfucking!WhichactuallyremindsmeofthereasonIcameoverheretoday!Howcomesyouhaven'tfuckedmymomyet!?"

Spike didn't know what to say, mainly because he hadn't understood a word that Pinkie had said, so he just went "Um... what?"

Pinkie rolled her eyes and said "You heard me! How comes you've fucked the moms of all of our friends but haven't paid a visit to mine yet?"

Pinkie stood up to let Spike get to his feet, as he dusted himself off, he went "Ugh... how do you know about that?" Had this been anyone else asking, he would have been nervous beyond belief with sweat rolling down his forehead and denying it, but Pinkie was different in that there weren't many things she took offense to, except for this particular moment where she was actually offended that Spike hadn't fucked her mom.

Pinkie just smiled and said "Pinkie sense of course! Recently my body has been giving me the same signs over and over again that signify one thing, that thing of course being you banging every single mom of every single one of our friends like you're on a MILF hunt! Though it seems you're taking your sweet time getting around to my mom and completing the list of "Moms of my friends that I've had sex with", so what gives?"

Spike held up his hands and went "Whoa whoa whoa hold up, your Pinkie sense tells you when I've had some kind of sex with a MILF that just happens to be a mom to one of our friends? What does your body do?"

Pinkie sighed and said "Well first my boobs lactate, then my ass hole clenches and then I'm hit with an orgasm out of nowhere that leaves my pussy soaked, so thanks to you I've had to change panties like a dozen times, but you're not answering my question!"

Spike decided not to press the issue and went "Well... I dunno, it's not like I was actually planning on having sex with all of them! Well... for the most part anyway... I guess I've just never had a reason to go and visit your mom just to have sex with her"

Pinkie smirked and said "Oh yeah? What if I gave you a reason?"

Spike was worried now, was Pinkie about to blackmail him into more MILF sex? He didn't know and he wasn't sure he wanted to find out, he liked sex a lot and he liked MILFs a lot, especially around the mating season, but the number of older women he had encountered with nothing better to do than have sex with him was getting ridiculous. Spike just went "One question... are you gonna keep harassing me to fuck your mom until I actually do it?"

Pinkie shrugged and went "I dunno, probably. That's not the reason though..."

Spike just walked past her and said "I'll find out the reason when I get to the rock farm, one thing I don't need during the mating season is a hyperactive girl bugging me to bang her mom, so you refusing to leave me alone until I fuck your mom is reason enough, let's go"

• 1 hour later -

"Thanks for agreeing to fuck my mom Spike, didn't want her being left out after all" said Pinkie.

As they were both making their way to Pinkie's old home on the rock farm, Spike went "Well you didn't really give me much of a choice Pinkie, so tell me, what's this special reason for me fucking your mom?"

Pinkie went "Well when it comes to sex, my parents are very vanilla and boring! My mom confessed to me a while ago that if she couldn't get my dad to try out the exotically erotic or the erotically exotic that she'd happily let someone else do it! From that day on I've been looking for someone special that I trust to help my mom live out her fantasies and cheat on my dad, cool huh!?" Spike often questioned Pinkie's sanity, the fact that she was actively excited about helping her mom have an affair just so she could experience the more exciting aspects of sex and had even called her mom to let her know that she and Spike were on the way was yet another tick in the "yes" column for the question "Is Pinkie crazy?" They knocked on the front door and, almost immediately, Cloudy Quartz opened the door to let them in.

Cloudy Quartz looked at Pinkie and said "Your father and sisters are in the south field, be a dear and go keep them distracted will you? It doesn't matter what you do, help them with the rock farming, suck off your father, let him spank you, fuck your sisters while he watches and jacks off, I don't care. You go and do whatever is necessary to keep them busy and occupied so that there is plenty of time for me to have some fun with your dragon friend, alright?"

Pinkie smiled and said "Okie dokie lokie! I'll make them stay put as long as I can" before skipping off to make sure Spike and her mother got to enjoy some privacy and alone time.

Cloudy Quartz ushered Spike in and, rather matter-of-factly, said "I assume you are here for some fun? At least I certainly hope so, sex between my husband and I has become stale, he's old-fashioned, traditional and frankly rather dull in the bedroom. I however, want to try new things"

Spike just nodded and went "Yep, that's why I'm here, though no offense, it's mostly to make sure Pinkie doesn't keep bothering me about it"

Cloudy Quartz gave a nod and said "Understandable, I am no not so unaware and desensitized to my daughter that I don't recognize that she can be a pain in the ass, though I digress, shall we move on to the bedroom?" Spike nodded, he wasn't particularly fond that this exchange was feeling a little clinical, like it was more of a business meeting than a quick hook-up, but if sex was the end result then he didn't really mind how they reached that end result. They both sat on the bed and Cloudy Quartz went "So Spike, you are here to help me indulge in a sexual activity that my husband won't engage in, but never let it be said that I am a selfish woman. If there is some kind of sexual gratification that I can grant you that you don't expect to receive from someone else, tell me what it is and a shall do it for you, no questions asked"

That statement gave Spike pause, this was a rare opportunity to enjoy something that he had yet to experience with a woman and probably an opportunity that was unlikely to ever come up again, he thought carefully about what to ask Cloudy Quartz to do for him until one particular sexual activity entered his mind that had always interested him but that he had yet to try out, he assumed most girls would find it a strange request and would say "no" before even really thinking about it. Spike swallowed the lump in his throat and said "I don't suppose you could give me a foot job could you?"

Cloudy Quartz didn't even flinch, she simply went "Of course, you can even finish on my feet if you like, cover my toes with your hot sticky cum..."

Spike's junk had already begun engorging steadily on his journey from the train to the house, but those words stoked the flames of lust in his loins and brought him once again to an angrily throbbing and stiff erection, the trademark of a dragon during the mating season. Cloudy Quartz gave a small smile and began undressing, her skin looked smooth to the touch, she had a decent pair of breasts on her and her ass wasn't too bad either, though Spike couldn't tell if her proportions were average or just ever so slightly above average, either way she looked extremely attractive for a woman her age. Cloudy Quartz tried to hide a blush as she saw Spike so openly ogling her body and saying "Well Spike... d-don't you think you ought t-to undress as well?" Spike woke from his stupor and quickly took off all of his clothes and cast them aside, Cloudy looked at his member and went "Hmm, not bad, not bad at all... now, how about you lie down and then I'll give a nice gentle foot job before we move on, won't that be nice and relaxing?" Spike just nodded and lied down on his back, propping up his torso with his elbows so he could see Cloudy take her place on the opposite side of the bed and stretch her legs out, wiggling her toes teasingly as her feet got closer and closer to his eagerly awaiting member.

When Cloudy's toes finally made contact with his prick, he shuddered both in arousal but also from how surprisingly cold her toes were, they weren't cold in a bad way, in fact the relative contrast in temperature between his very warm cock and her cool feet seemed to almost relax him in some way, like the raging fire of his lust had been reduced to a calm yet brightly shining pile of embers. Rather skillfully, Cloudy started moving her feet up and down, her toes adequately gripping Spike's dick and pumping him almost as well as a hand would do, either Cloudy had done this before or had just watched a lot of porn. Spike breathed heavily as Cloudy calmly kept up the steady and rhythmic movement of her feet, being sure to tense and flex her toes every so often to make sure Spike was staying consistently hard enough to be enjoying the foot job she was delivering, even though the way she was doing the foot job showed that she wasn't being at all awkward or clumsy with it. She was good at it and she knew it, it was so perfect it almost felt as if she had practiced in advance in case she had to, one day, do this for a guy who was into that sort of thing.

As Spike's breathing became rapid and the stirrings of an orgasm built in his groin, Cloudy moved from just using her toes to holding Spike's cock in the soft and smooth arches of her feet and increased her speed, focusing on bringing Spike to the edge before pushing him to the tipping point and getting him to release his load. Steam began to rise from Spike's nostrils, this foot job was a new and very pleasurable experience, he was enjoying it far more than he expected to and he found it a challenge to hold back his moans of enjoyment and stave off his orgasm until the last second. Eventually, Spike gave in and let out a series of grunts as his cock pumped out rope after rope of hot jizz, every single one landing on the feet that had so lovingly caressed his achingly hard erection. Throughout the entirety of his ejaculation, Cloudy, rather than stopping or slowing down, simply kept going, her feet carrying on their relentless movement along his dick.

Even after Spike had clearly finished firing off his load, Cloudy still felt the need to carry on stimulating him with her feet, Spike appreciated that she was so intent on pleasing him as fully as possible but had to stop her, every available centiliter of spunk he had available in that load had been delivered, both onto her feet and down the length of his cock, he was very much in a comfort zone but didn't want Cloudy to push him into the territory of being slightly uncomfortable to downright utter discomfort from lack of a break. "Nng... Cloudy, you can stop now..."

Without stopping whatsoever, she simply said "Can you promise me you'll stay hard after I stop?"

Spike went "Yes yes, I promise, erections are par for the course during the mating season and considering you're still jacking me off with your feet after I've already cum, it's almost guaranteed that I'm not going soft any time soon", Cloudy, luckily, accepted that answer and removed her feet from his cock.

After getting off the bed to make a quick visit to the bathroom to clean up her feet, she returned and said "So Spike, have you regained enough energy for more?"

Spike let out a breath and went "Phew... I think so..."

Cloudy smiled and said excellent as she opened a nearby cupboard and started digging around for something, "You know, I'm surprised that you so willingly agreed to this Spike, I know that it was partly to get Pinkie Pie to leave you alone but not many guys would even dare to think about trying pegging", Spike's eyes went wide and his ears flexed, had he heard that right? He couldn't think of any other word it could be, this was definitely going where he thought it was going but he felt a futile need to clarify what he had heard, just in case.

Quietly, he said "Did you say... p-p-pegging?"

When Cloudy turned around to face him with a bottle of lube in one hand and what was very clearly a strap-on in the other, she looked at him slightly quizzically and said "Well... yes of course, I had assumed Pinkie told you that this was what I wanted to try out, I told her over the phone... did she not...?" Spike shook his head, Pinkie hadn't said a word about pegging. Cloudy groaned and said "That blasted girl! I told her that I needed a guy who was willing to give pegging a go! I told her time and time again! Ugh... look, I'm so sorry Spike, I'll just... put this stuff away and..."

Spike quickly went "No no don't! I mean... it's just unexpected, I'm not necessarily saying no......"

Cloudy, with a hint of excitement went "Does that mean you'll try it?" Cloudy waited with bated breath as Spike pondered his response, she hoped beyond hope that he would say yes, this might have been her only chance to try pegging out on someone and she didn't want it to pass her by. Spike thought for a good hard minute, he knew what pegging was and why some guys liked it but he had never actually considered it himself, so he was apprehensive to say the least, but then again he remembered that the whole reason he was here was to help Cloudy explore her sexuality and it wouldn't really be fair for him to say no, especially after such an awesome foot job that she was not in any way obligated to do for him. Of course there was also the added bonus of getting Pinkie to shut the fuck up for once in her life.

Spike took in a deep breath and let it out before saying "Yes Cloudy, I'll let you peg me"